I actually prefer to photograph outside when it is cloudy or overcast. The light on a overcast day is usually beautiful and soft. The trick is to be out early in the day. The later is gets, the darker it gets and this can be trouble. Here is an image I created of Alana on an overcast day last fall.

Now you may be thinking that you'll only want to have your session outside on an overcast day. That's not necessarily the case. I'm pretty good at finding spots that are a kind of substitute for cloud cover. As long as we're near some sort of building or structure, even on a bright sunny day, we can find great spots with great light. Here is an image I created in the middle of a very sunny day, just a few weeks ago. I think that the lighting on Amanda's face (below) is killer.

Of course, when it's raining, it is pretty tough to have an outdoor session. Typically, when a client schedules something outside, we choose an alternate date in case of rain. However, sometimes, the rain adds to the photo. Check out this photo of kids playing in the rain.

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